Research Progress in Study of Isowurtzitane Derivatives

doi:10.6023/cjoc1104225

Abstract

Hexanitrohexaazaisowurtzitane (HNIW or CL-20) is presently the most powerful energetic compound in the world. The synthesis of CL-20 or cage molecules has attracted considerable interest of experts in the area of high-energy materials over the last two decades, and more than 100 isowurtzitane derivatives were synthesized. In this paper, the synthesis, application and reactivity of these compounds are summarized systematically according to different substituents on the cage and types of reactions. The developing tends of isowurtzitane derivatives are also presented.

Key words: isowurtzitane derivatives, high energy density compound, review

Cite this article

Gong Xubin, Sun Chenghui, Pang Siping, Zhang Jing, Li Yuchuan, Zhao Xinqi . Research Progress in Study of Isowurtzitane Derivatives[J]. Chin. J. Org. Chem., 2012, (03): 486-496.

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References

[1] Qiu, L. M.; Gong, X. D.; Zheng, J.; Xiao, H. M. J. Hazard. Mater.2009, 166, 931.

[2] Lauderdale, W. J.; Slwell, W. A. Air Force Astronautics Laboratory,Report AFAL CP-87-002, September, 1987, and subsequentreports.

[3] Nielsen, A. T.; Nissan, R. A.; Vanderah, D. J. J. Org. Chem. 1990,55, 1459.

[4] Zhang, M. X.; Eaton, P. E.; Gilardi, R. Angew. Chem., Int. Ed.2000, 39, 401.

[5] Simpson, R. L.; Urtiew, P. A.; Ornellas, D. L.; Moody, G. L.;Scribner, K. J.; Hoffmann, D. M. Propellants, Explos., Pyrotech.1997, 22, 249.

[6] Nielsen, A. T. US 5693794, 1997 [Chem. Abstr. 1997, 128, 36971].

[7] Klapötke, T. M.; Krumm, B.; Piotrowski, H.; Polborn, K.; Holl, G.Chem. Eur. J. 2003, 9, 687.

[8] Kerscher, T.; Klapötke, T. M.; Krumm, B.; Polborn, K.; Scherr, M.J. Fluorine Chem. 2006, 127, 1030.

[9] Gottlieb, H. E.; Cohen, S.; Gottlieb, L. Chem. Eur. J. 2010, 16,5568.

[10] Cagnon, G.; Eck, G.; Herve, G.; Jacob, G. US 7279572, 2004 [Chem. Abstr. 2004, 142, 6566].

[11] Li, X. L.; Sun, C. H.; Zhao, X. Q.; Song, J. W. Chin. J. Energ. Mater.2007, 15, 490 (in Chinese).(李新乐, 孙成辉, 赵信岐, 宋建伟, 含能材料, 2007, 15, 490.)

[12] Adamiak, J.; Maksimowski, P. Propellants, Explos., Pyrotech.2009, 34, 315.

[13] Chapman, R. D.; Hollins, R. A. J. Energ. Mater. 2008, 26, 246.

[14] (a) Han, W. R.; Ou, Y. X.; Liu, J. Q.; Wang, G. L. Chin. Chem.Lett. 2004, 15, 1153.(b) Han, W. R.; Ou, Y. X.; Liu, J. Q.; Chen, B. R. Chin. J. Org.Chem. 2005, 25, 1259 (in Chinese).(韩卫荣, 欧育湘, 刘进全, 陈博仁, 有机化学, 2005, 25, 1259.)

[15] Huang, X. M. S. Thesis, Beijing Institute of Technology, Beijing,2005 (in Chinese).(黄兴, 硕士论文, 北京理工大学, 北京, 2005.)

[16] Han, W. R.; Ou, Y. X.; Zhang, X. H.; Huang, X.; Mou, W.; Gao, Y.L. Chin. J. Energ. Mater. 2008, 16, 153 (in Chinese).(韩卫荣, 欧育湘, 张雪红, 黄兴, 牟微, 高岩磊, 含能材料,2008, 16, 153.)

[17] Wardle, R. B.; Hinshaw, J. C. US 7129348, 2006 [Chem. Abstr.2006, 145, 438653].

[18] Lu, L. Y.; Ou, Y, X.; Wang, J. L. Fine Chem. 2004, 21, 321 (inChinese).(吕连营, 欧育湘, 王建龙, 精细化工, 2004, 21, 321.)

[19] Wang, C.; Ou, Y. X.; Wang, J. L. Chem. World 2000, 9, 462 (inChinese).(王才, 欧育湘, 陈博仁, 化学世界, 2000, 9, 462)

[20] Yang, Z. Y. Ph.D. Dissertation, Beijing Institute of Technology,Beijing, 1995 (in Chinese).(杨宗云, 博士论文, 北京理工大学, 北京, 1995.)

[21] Kodama, T.; Minoura, H.; Miyake, N.; Yamamatus, S.; Katsumata,T. WO 98/16529, 1998 [Chem. Abstr. 1998, 129, 6228].

[22] Bellamy, A. J. Tetrahedron 1995, 51, 4711.

[23] Ou, Y, X.; Xu, J. Q.; Chen, J. T.; Chen, B. R.; Zheng, F. P.; Jia, H.P.; Wang, C. Chem. J. Chin. Univ. 1999, 20, 561 (in Chinese).(欧育湘, 徐永江, 陈江涛, 陈博仁, 郑福平, 贾会平, 王才, 高等学校化学学报, 1999, 20, 561.)

[24] Wardle, R. B.; Edwards, W. W. WO 97/20785, 1997 [Chem. Abstr.1997, 127, 110983].

[25] Qiu, W. G.; Chen, S. S.; Yu, Y. Z. Chin. J. Chem. 1999, 17, 554.

[26] Chen, S. S.; Qiu, W. G.; Yu, Y. Z. Acta Armamentarii 2000, 21,116 (in Chinese).(陈树森, 邱文革, 于永忠, 兵工学报, 2000, 21, 116.)

[27] Chen, S. S.; Qiu, W. G.; Yu, Y. Z. Chin. J. Explos. Propellants2000, 23, 11 (in Chinese).(陈树森, 邱文革, 于永忠, 火炸药学报, 2000, 23, 11.)

[28] Qiu, W. G.; Chen, S. S.; Yu, Y. Z. Chin. J. Synth. Chem. 2002, 10,220.

[29] Qiu, W. G.; Chen, S. S.; Yu, Y. Z. Chin. J. Explos. Propellants2001, 24, 62 (in Chinese).(邱文革, 陈树森, 于永忠, 火炸药学报, 2001, 24, 62.)

[30] Pang, S. P.; Yu, Y. Z.; Zhao, X. Q. Acta Armamentarii 2002, 23,276 (in Chinese).(庞思平, 于永忠, 赵信岐, 兵工学报, 2002, 23, 276.)

[31] Liu, J. Q.; Chen, S. S.; Yu, Y. Z.; Zhao, X. Q. Chin. J. ExplosivesPropellants 2003, 26, 5 (in Chinese).(刘江强, 陈树森, 于永忠, 赵信岐, 火炸药学报, 2003, 26, 5.)

[32] Pang, S. P.; Yu, Y. Z.; Zhao, X. Q. Propellants, Explos., Pyrotech.2005, 30, 442.

[33] Li, Y. Y.; Wang, L.; Lin, Q. H.; Ma, Q. L.; Pang, S. P.; Yu, Y. Z. J.Beijing Institute Technol. 2010, 19, 476.

[34] Liu, J. Q.; Chen, S. S.; Yu, Y. Z.; Zhao, X. Q. Chin. J. Energ. Mater.2002, 10, 145 (in Chinese).(刘江强, 陈树森, 于永忠, 赵信岐, 含能材料, 2002, 10, 145.)

[35] (a) Liu, L. H.; Ou, Y. X.; Chen, B. R.; Xu, Y. J.; Lei, X. Y. Chin. J.Explos. Propellants 2000, 23, 50 (in Chinese).(刘利华, 欧育湘, 陈博仁, 徐永江, 雷向阳, 火炸药学报, 2000,23, 50.)(b) Liu, L. H.; Ou, Y. X.; Wang, J. Q.; Chen, B. R.; Lei, X. Y.Chin. J. Explos. Propellants 2001, 24, 16 (in Chinese).(刘利华, 欧育湘, 王建全, 陈博仁, 雷向阳, 火炸药学报, 2001,24, 16.)

[36] Liu, J. Q.; Ou, Y. X. Acta Armamentarii, 2006, 27, 920(in Chinese).(刘进全, 欧育湘, 兵工学报, 2006, 27, 920.)

[37] Wu, X. G.; Wang, Y. F.; Ou, Y. X.; Liu, J. Q. Chin. J. Energ. Mater.2006, 14, 343 (in Chinese).(吴相国, 王艳飞, 欧育湘, 刘进全, 含能材料, 2006, 14, 343.)

[38] Lu, L. Y.; Ou, Y. X.; Wang, J. L.; Chen, B. R. Fine Chem. 2003,20, 577(in Chinese).(吕连营, 欧育湘, 王建龙, 陈博仁, 精细化工, 2003, 20, 577.)

[39] Kodama, K.; Masahiro, T.; Masanori, I. WO 96/23792, 1996 [Chem. Abstr. 1996, 125, 275920].

[40] Qian, H.; Ye, Z. W.; Lv, C. X. Lett. Org. Chem. 2007, 4, 482.

[41] Pang, S. P.; Yu, Y. Z.; Zhao, X. Q. Chin. J. Explos. Propellants2002, 25, 27 (in Chinese).(庞思平, 于永忠, 赵信岐, 火炸药学报, 2002, 25, 27.)

[42] Pang, S. P.; Yu, Y. Z.; Zhao, X. Q. Chin. J. Energ. Mater. 2002, 10,1 (in Chinese).(庞思平, 于永忠, 赵信岐, 含能材料, 2002, 10, 1.)

[43] Liu, J. Q.; Chen, S. S.; Yu, Y. Z.; Zhao, X. Q. Chin. J. Explos.Propellants 2003, 26, 60 (in Chinese).(刘江强, 陈树森, 于永忠, 赵信岐, 火炸药学报, 2003, 26, 60.)

[44] Hamilton, R. S.; Sanderson, A. J.; Wardle, R. B.; Warner, K. F. InProceedings of 31st International Annual Conference of ICT,Karlsruhe, 2000, p. 21-1.

[45] Cannizzo, L.; Hamilton, S.; Sanderson, A.; Wardle, R.; White, S. InProceedings of 32st International Annual Conference of ICT, 2000,p. 108-1.

[46] Bellamy, A. J.; MacCuish, A.; Golding, P.; Mahon, M. F. Propellants,Explos., Pyrotech. 2007, 32, 20.

[47] Fang, T.; Sun, C. H.; Zhao, X. Q. Chin. J. Energ. Mater. 2004, 12,291 (in Chinese).(方涛, 孙成辉, 赵信岐, 含能材料, 2004, 12, 291.)

[48] Sun, C. H.; Fang, T.; Yang, Z. Y.; Bai, J. H.; Feng, Z. W.; Liu, J.;Li, L.; Ma, C. P.; Chen, Z. L.; Zhao, X. Q. Chin. J. Energ. Mater.2009, 17, 161 (in Chinese).(孙成辉, 方涛, 杨宗云, 白军红, 冯泽旺, 刘娟, 李莉, 马鹏常,陈联忠, 赵信岐, 含能材料, 2009, 17, 161.)

[49] Chen, L. Q. M. S. Thesis, Beijing Institute of Technology, Beijing,2008 (in Chinese).(陈留群, 硕士论文, 北京理工大学, 北京, 2008.)

[50] He, J. M. S. Thesis, Beijing Institute of Technology, Beijing, 2009(in Chinese).(贺晶, 硕士论文, 北京理工大学, 北京, 2009.)

[51] Shi, R. M. S. Thesis, Beijing Institute of Technology, Beijing, 2008 (in Chinese).(施瑞, 硕士论文, 北京理工大学, 北京, 2008.)

[52] Cai, S. L. M. S. Thesis, Beijing Institute of Technology, Beijing,2008 (in Chinese).(蔡水兰, 硕士论文, 北京理工大学, 北京, 2008.)

[53] Sun, C. H.; Zhao, X. Q.; Li, Y. C.; Pang, S. P. Chin. Chem. Lett.2010, 21, 572.

[54] Bellamy, A. J.; MacCuish, A.; Golding, P. Propellants, Explos.,Pyrotech. 2003, 28, 157.

[55] Lukyanov, O. A.; Shlykova, N. I. Russ. Chem. Bull. Int. Ed. 2004,53, 566.

[56] Duddu, R.; Dave, P. R.; Damavarapu, R.; Surapaneni, R.; Gilardi,R. Synth. Commun. 2005, 35, 2709.

[57] Wu, Y. K.; Ou, Y. X.; Liu, J. Q.; Chen, B. R. Propellants, Explos.,Pyrotech. 2004, 29, 155.

[58] Meng, Z.; Ou, Y. X.; Liu, J. Q.; Wang, Y. F. Chin. J. Explos. Propellants2006, 29, 65 (in Chinese).(孟征, 欧育湘, 刘进全, 王艳飞, 火炸药学报, 2006, 29, 65.)

[59] Duddu, R.; Dave, P. R.; Damavarapu, R.; Surapaneni, R.; Gilardi,R.; Parrish, R. Synth. Commun. 2008, 38, 767.

[60] 陈福波, 段宝如, 于永忠, 兵器工业部二一四所研究报告汇编,1980, pp. 29～33.

[61] Ramekrishnan, V. T.; Vedachalam, M.; Boyer, J. H. Heterocycles1990, 31(3), 478.

[62] Highsmith, T. K.; Edwards, W. W.; Wardle, R. B. US 5498711,1995 [Chem. Abstr. 1995, 122, 290890].

[63] Sanderson, A. J.; Hajik, R. M.; Highsmith, T. K.; Johnston, H. E.US 6512113, 2003 [Chem. Abstr. 2003, 138, 124633].

[64] Li, Z. X.; Ou, Y. X.; Chen, B. R. Chin. J. Energ. Mater. 2001, 9,104 (in Chinese).(李战雄, 欧育湘, 陈博仁, 含能材料, 2001, 9, 104. )

[65] Xu, R.; Zhou, X. Q.; Zeng, G. Y.; Liu, C. Chin. J. Explos.Propellants 2006, 29, 26(in Chinese).(徐容, 周小青, 曾贵玉, 刘春, 火炸药学报, 2006, 29, 26.)

[66] Jacob, G; Lacroix, G; Destombes, V. In Proceedings of 31st InternationalAnnual Conference of ICT, Karlsruhe, 2000, pp. 106-1～106-12.

[67] Gatilov, Y. V.; Rybalova, T. V.; Efimov, O. A.; Lobanova,; A. A.;Sakovich, G. V.; Sysolyatin, S. V. J. Struct. Chem. 2005, 46, 566.

[68] Sun, C. H.; Zhao, X. Q. J. Chem. Crystallogr. 2006, 36, 255.

[69] Sun, C. H.; Zhao, X. Q. Chin. J. Energ. Mater. 2008, 16, 669 (inChinese).(孙成辉, 赵信岐, 含能材料, 2008, 16, 669.)

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